JPS6314709B2 - - Google Patents
Info
- Publication number
- JPS6314709B2 JPS6314709B2 JP57142768A JP14276882A JPS6314709B2 JP S6314709 B2 JPS6314709 B2 JP S6314709B2 JP 57142768 A JP57142768 A JP 57142768A JP 14276882 A JP14276882 A JP 14276882A JP S6314709 B2 JPS6314709 B2 JP S6314709B2
- Authority
- JP
- Japan
- Prior art keywords
- nitrobenzaldehyde
- diacylate
- dihydropyridine
- nitrophenyl
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- COLPLFZHPXIFCQ-UHFFFAOYSA-N 1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=CNC=C(C(O)=O)C1 COLPLFZHPXIFCQ-UHFFFAOYSA-N 0.000 description 1
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU2005/81A YU41983B (en) | 1981-08-19 | 1981-08-19 | Process for preparing 1,4-dihydro-pyridine derivatives |
| YU2005/81 | 1981-08-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5839663A JPS5839663A (ja) | 1983-03-08 |
| JPS6314709B2 true JPS6314709B2 (sv) | 1988-04-01 |
Family
ID=25556467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57142768A Granted JPS5839663A (ja) | 1981-08-19 | 1982-08-19 | ４−（２′−ニトロフエニル）−２，６−ジメチル−３，５−ジカルブメトキシ−１，４−ジヒドロ−ピリジンの製造方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4467093A (sv) |
| JP (1) | JPS5839663A (sv) |
| AT (1) | AT380876B (sv) |
| CA (1) | CA1185243A (sv) |
| CH (1) | CH651297A5 (sv) |
| DK (1) | DK155734C (sv) |
| ES (1) | ES515063A0 (sv) |
| FI (1) | FI74275C (sv) |
| NL (1) | NL8203260A (sv) |
| PL (1) | PL131222B1 (sv) |
| SE (1) | SE441743B (sv) |
| SU (1) | SU1099842A3 (sv) |
| YU (1) | YU41983B (sv) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02118009U (sv) * | 1989-03-09 | 1990-09-21 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4771057A (en) * | 1986-02-03 | 1988-09-13 | University Of Alberta | Reduced pyridyl derivatives with cardiovascular regulating properties |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670827C3 (de) * | 1967-03-20 | 1974-10-24 | Bayer Ag, 5090 Leverkusen | 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin |
| DE2808930A1 (de) * | 1978-03-02 | 1979-09-06 | Bayer Ag | Verfahren zur herstellung von 2-nitrobenzaldehyd |
| JPS554318A (en) * | 1978-06-23 | 1980-01-12 | Asahi Chem Ind Co Ltd | Preparation of 1,4-dihydropyridine |
| JPS5520719A (en) * | 1978-07-31 | 1980-02-14 | Asahi Chem Ind Co Ltd | Preparation of 1,4-dihydropyridine derivative |
| JPS55124760A (en) * | 1979-03-16 | 1980-09-26 | Kanebo Ltd | Preparation of 1,4-dihydropyridine derivative or its salt |
-
1981
- 1981-08-19 YU YU2005/81A patent/YU41983B/xx unknown
-
1982
- 1982-07-27 US US06/402,487 patent/US4467093A/en not_active Expired - Fee Related
- 1982-07-29 CA CA000408333A patent/CA1185243A/en not_active Expired
- 1982-08-11 SE SE8204658A patent/SE441743B/sv not_active IP Right Cessation
- 1982-08-11 AT AT0307082A patent/AT380876B/de not_active IP Right Cessation
- 1982-08-16 FI FI822842A patent/FI74275C/sv not_active IP Right Cessation
- 1982-08-17 CH CH4929/82A patent/CH651297A5/de not_active IP Right Cessation
- 1982-08-17 PL PL1982237935A patent/PL131222B1/pl unknown
- 1982-08-17 ES ES515063A patent/ES515063A0/es active Granted
- 1982-08-18 DK DK370382A patent/DK155734C/da not_active IP Right Cessation
- 1982-08-18 SU SU823482656A patent/SU1099842A3/ru active
- 1982-08-19 NL NL8203260A patent/NL8203260A/nl not_active Application Discontinuation
- 1982-08-19 JP JP57142768A patent/JPS5839663A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02118009U (sv) * | 1989-03-09 | 1990-09-21 |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8204658L (sv) | 1983-02-20 |
| FI74275B (fi) | 1987-09-30 |
| SE8204658D0 (sv) | 1982-08-11 |
| YU41983B (en) | 1988-04-30 |
| YU200581A (en) | 1984-02-29 |
| DK370382A (da) | 1983-02-20 |
| US4467093A (en) | 1984-08-21 |
| JPS5839663A (ja) | 1983-03-08 |
| ATA307082A (de) | 1985-12-15 |
| CH651297A5 (de) | 1985-09-13 |
| DK155734B (da) | 1989-05-08 |
| FI822842A0 (fi) | 1982-08-16 |
| CA1185243A (en) | 1985-04-09 |
| FI74275C (sv) | 1988-01-11 |
| AT380876B (de) | 1986-07-25 |
| ES8306364A1 (es) | 1983-06-01 |
| FI822842L (fi) | 1983-02-20 |
| SU1099842A3 (ru) | 1984-06-23 |
| DK155734C (da) | 1989-09-25 |
| NL8203260A (nl) | 1983-03-16 |
| ES515063A0 (es) | 1983-06-01 |
| SE441743B (sv) | 1985-11-04 |
| PL131222B1 (en) | 1984-10-31 |
| PL237935A1 (en) | 1983-02-28 |
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